If you’re looking for a charming New England town with great food, river views, and local flavor, I always say—don’t skip Middletown, Connecticut. I’ve explored its downtown, walked its riverside paths, and sampled meals that honestly caught me by surprise. It’s one of those places where college town energy (thanks to Wesleyan University) meets small-town friendliness—and I think you’ll feel that mix the moment you arrive.
Since it's a 2+ hour drive from NYC, I recommend spending the night so that you are not rushing.
Top Things to Do in Middletown, Connecticut
- Stroll along the Connecticut River at Harbor Park – I’ve taken peaceful walks here and even caught a boat tour or two. The views are beautiful, especially in the fall when the leaves are glowing.
- Explore Main Street – I always make time for downtown Middletown. You’ll find independent shops, great coffee spots, and a food scene that punches well above its weight. I’ve had amazing sushi, Indian food, and craft cocktails—all within a few blocks.
- Visit Wadsworth Falls State Park – I’ve hiked the trails here and cooled off by the falls in summer. It’s a quiet, easy escape into nature just minutes from town.
- Tour Wesleyan University – Whether I’m walking the leafy campus or popping into the art galleries and theaters, Wesleyan always feels lively and inspiring. You’ll sense the creativity everywhere.
- Catch a show at The Buttonwood Tree Performing Arts Center – I love this spot for music, storytelling, and open mic nights. It’s small, intimate, and full of local heart.
- Visit Kidcity Children’s Museum – When I’ve had little ones in tow, this place is a lifesaver. It’s playful, hands-on, and made just for kids to explore and imagine.
Best Time to Visit Middletown, CT
In my experience, spring and fall (April–June and September–October) are the most beautiful times to visit. The weather is perfect for outdoor walks and café hopping, and the fall foliage is truly something else. Summer has a relaxed vibe, and you’ll find live music and riverfront events. I’ve even visited in winter and found the downtown still cozy—especially with a warm bowl of ramen or coffee in hand.
How to Get to Middletown, CT
- By Car: I usually take Route 9 or I-91—it’s a scenic drive whether you’re coming from Hartford (about 30 minutes) or New Haven (about 40 minutes).
- By Train: There’s no direct train to Middletown, but I’ve taken Amtrak or Metro-North to New Haven or Meriden, then grabbed a rideshare or rental car. It’s a smooth connection.
- By Air: Bradley International Airport (BDL) near Hartford is the closest major airport. I’ve flown in and out of there and found it easy to navigate, just under an hour’s drive away.
Where to Stay in Middletown, CT
- Inn at Middletown – I’ve stayed here and loved the classic charm. It’s in the heart of downtown, walking distance to everything, with cozy rooms and a welcoming vibe.
- Airbnb Options – I’ve found some lovely local homes and apartments to rent, especially near Wesleyan or tucked into quiet residential streets. Great if you want a more personal, homey stay.
- Nearby Hotels in Cromwell or Meriden – If you’re looking for chain hotels with extra space or easy highway access, I’ve stayed just a few minutes outside Middletown and still been close to everything.
Best Things to Do in Middletown, CT
Kidcity Children's Museum
The Kidcity Children's Museum is made up of three floors offering all manner of imaginative play for children between the ages of one and seven, along with their families. Every exhibit at the museum is unique and handmade, created by Kidcity’s in-house artists who are passionate about inspiring playfulness in people of all ages. Exhibits include the Fishery, in which children can use pulley baskets and conveyors to bring in that day’s catch; the Middleshire, a tiny medieval village where children can construct a castle; and the Space Age Roadtrip, during which friendly aliens travel along Route 66.
119 Washington St, Middletown, CT 06457, Phone: 860-347-0495
Wadsworth Falls State Park
The Wadsworth Falls State Park provides visitors with various trails for biking and hiking throughout the park, as well as a chance to enjoy a beautiful waterfall. Guests in the state park can also use the picnic area and the designated area for swimming. Visitors wanting to swim or have a picnic in Wadsworth Falls State Park should keep in mind that picnicking and swimming is not allowed around the Big Falls, as the area is meant for only short visits of people viewing the scenic waterfall. The falls can viewed by taking the path from the parking lot on Cherry Hill Road.
721 Wadsworth St, Middletown, CT 06457
Attractions for Couples
Wesleyan University
Wesleyan University in Middletown, Connecticut was established back in the year 1831 and is an energetic and diverse community for the liberal arts, a place where practical idealism and critical thinking go together. The 316-acre historic and beautiful New England campus provides a comfortable, collaborative, and intimate environment for learning that is supported by unique opportunities for research, cutting-edge facilities, and renowned faculty. Wesleyan University is a two-hour scenic drive from both the cities of Boston and New York City, nestled within the heart of the state of Connecticut and open for visitors to come and explore.
45 Wyllys Ave, Middletown, CT 06459, Phone: 860-685-2000
Empower Leadership Sports & Adventure Center
The Empower Leadership Sports & Adventure Center is the only fully-guided zipline tours in southern New England. The adventure center has a number of thrilling outdoor adventures that visitors can choose from, such as scavenger hunts, compass, navigation, more than half a mile of ziplining, aerial adventures, combination adventures, and tree climbing. The Empower Leadership Sports and Adventure Center features 2,500 feet of zip lines, with many different options to choose from, including moonlight zipline tours, which are available monthly. The center offers exciting and memorable outdoor adventures experiences for visitors of all levels of experience.
2011 S Main St, Middletown, CT 06457, Phone: 860-638-4754
General Mansfield House
The General Mansfield House serves as the headquarters for the Middlesex County Historical Society and is of the few remaining residential structures standing along Main Street of Middletown, Connecticut. The historic house was constructed by Catherine and Samuel Livingston Mather in the year 1817. Their daughter, Louisa, married Joseph Mansfield. Generations of the family lived in the house until it became the society’s headquarters in 1959. The garden in the front features a formal herb garden, along with a border of fragrant lilacs during the spring. Behind the General Mansfield House is the Rose Garden with several different varieties.
151 Main St, Middletown, CT 06457, Phone: 860-346-0746
Recommended Activities for Families
Van Vleck Observatory
The Van Vleck Observatory is owned and operated by the Wesleyan University in Middletown, constructed back in 1914. The astronomical observatory is named for John M. Van Vleck, a former head professor for the university’s Department of Mathematics and Astronomy. The Van Vleck Observatory contains three telescopes. The 16-inch telescope and the 20-inch telescope are used during the public observation nights each week, which are open to the general public. The third telescope housed inside of the Van Vleck Observatory is a 24-inch Perkins Telescope, used mostly for research purposes. The Perkins Telescope is one of the New England region’s largest telescopes.
96 Foss Hill, Middletown, CT 06459, Phone: 860-685-2130
Artfarm
Artfarm is a non-profit, independent organization that was established in 2001. The arts organization is committed to producing high quality theater performances with a commitment as well to social action, environmental sustainability, and simple living. ARTFARM is focused on the ideas of open space and farm preservation, and the rising rate of developers consuming the precious lands in Connecticut is of great concern to the organization. As a result, ARTFARM is a small working organic farm, a theater, and a workshop and retreat center where artists, underserved youth, activists, and simply good people can come for inspiration and renewal.
119 Highland Ave, Middletown, CT 06457, Phone: 860-346-4390
Dart Island State Park
Dart Island State Park, technically located in the town of Middletown, Connecticut, is a recreation area open to the general public. The state park is made up of approximately nineteen acres of undeveloped land on a sandbar island. Dart Island State Park is situated in the middle of the Connecticut River and can only be reached by boat. This sandbar island features a wooded area filled with what are described as “typical river trees,” such as red maple, poplar, and willow. Dart Island State Park has no public facilities, and is often used for fishing, boating, and bird watching.
Middletown, CT 06457, Phone: 860-424-3200
Where to Eat:
Taino Smokehouse
The Taino Smokehouse is a small place with quite a bit of heart focusing on the craft of providing quality barbecue and hospitality. The little smokehouse uses just a few natural simple elements, fire, pepper, and salt to make their barbecue. Taino Smokehouse works hard to offer the purist barbecue anywhere within the Northeast. Hospitality is the main goal of the full-service restaurant, striving to make sure every guest feels like family when they come in. Taino Smokehouse waits until the fire in the pit begins to produce a hot blue smoke before putting the barbecue on the pit.
482 South Main St, Middletown, CT 06457, Phone: 860-358-9828
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